Tetrahydrofuran → tert-Butyl (1S,2S)-1-amino-2-ethylcyclopropane-1-carboxylate

HRID 969962Notes

Reaction equation

HRID 969962 reaction equation
[C:1]([O:5][C:6]([C@:8]1([NH:13]C(OCC[Si](C)(C)C)=O)[CH2:10][C@@H:9]1[CH2:11][CH3:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].CCCC[N+](CCCC)(CCCC)CCCC.[F-].C1COCC1>CCOC(C)=O>[C:1]([O:5][C:6]([C@:8]1([NH2:13])[CH2:10][C@@H:9]1[CH2:11][CH3:12])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 2724141Tetrabutylammonium FluorideHCID 86601847(1S,2S) 2-Ethyl-1-(2trimethylsilanylethoxycarbonylamino)cyclopropane-carboxylic acid tert-butyl ester

Product 1

HCID 86620254tert-Butyl (1S,2S)-1-amino-2-ethylcyclopropane-1-carboxylate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To the product of Step 3 (3 g, 9 mmol) was added a 1.0 M TBAF solution in THF (9.3 mL, 9.3 mmol) and the mixture heated to reflux for 1.5 h, cooled to rt and then diluted with 500 ml of EtOAc. The solution was successively washed with water (2×100 mL), brine (2×100 mL), dried (MgSO4), concentrated in vacuo to provide the title intermediate

Workup

  1. temperaturethe mixture heated
  2. temperatureto reflux for 1.5 h
  3. washThe solution was successively washed with water (2×100 mL), brine (2×100 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5a31458e6ce94b639883b395b5f31015
Source dataset
uspto-grants-2007_12
Patent number
US07309708B2

Reaction notes

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